TELOXANTRONE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H25N5O4.2ClH.H2O
Molecular Weight	502.391
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.Cl.Cl.CNCCNC1=C2C3=C(C=C1)N(CCNCCO)N=C3C4=C(O)C=CC(O)=C4C2=O

InChI

InChIKey=UMDBGTRUNWFBPE-UHFFFAOYSA-N

InChI=1S/C21H25N5O4.2ClH.H2O/c1-22-6-7-24-12-2-3-13-17-16(12)21(30)19-15(29)5-4-14(28)18(19)20(17)25-26(13)10-8-23-9-11-27;;;/h2-5,22-24,27-29H,6-11H2,1H3;2*1H;1H2

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C21H25N5O4
Molecular Weight	411.4543
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8262739 | https://www.ncbi.nlm.nih.gov/pubmed/8241002 | https://www.ncbi.nlm.nih.gov/pubmed/8241003 | https://adisinsight.springer.com/drugs/800000732

Teloxantrone (also known as DuP 937) was developed as an anthrapyrazole intercalator that inhibits DNA synthesis. Teloxantrone interacts with topoisomerase II, thereby inhibiting DNA replication and repair, as well as RNA and protein synthesis. The drug participated in phase II clinical trials in colorectal carcinoma, in non-small cell lung cancer, in metastatic malignant melanoma. However, these studied apparently were discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Phase I pharmacokinetic study of DUP-937, a new anthrapyrazole.	1993-11	8157472
A phase II trial of DuP 937 (Teloxantrone) in non-small cell lung cancer. A study of the NCIC Clinical Trials Group.	1993-09	8241002
A phase II study of DuP 937 (Teloxantrone) in metastatic malignant melanoma: a study of the National Cancer Institute of Canada Clinical Trials Group (NCICCTG).	1993-09	8241003
Phase II study on DuP 937 (Teloxantrone) in colorectal carcinoma. A Canadian National Cancer Institute Clinical Trial Group study.	1993-05-01	8262739
In vitro DNA strand scission and inhibition of nucleic acid synthesis in L1210 leukemia cells by a new class of DNA complexers, the anthra[1,9-cd]pyrazol-6(2H)-ones (anthrapyrazoles).	1985-10-01	2413861

Sample Use Guides

In Vivo Use Guide

A phase I trial was conducted in which DUP-937 (TELOXANTRONE) was given in an intravenous bolus weekly for 3 weeks. Cycles were repeated every 5 weeks. Twenty men and 13 women with median ECOG performance status of 1 completed 74 cycles. The starting dose was 0.55 mg/m2/week and doses were escalated to 16 mg/m2/week

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:21:12 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:12 GMT 2025`
Record UNII	7ZQK8VIO6V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TELOXANTRONE HYDROCHLORIDE

Official Name

English

DUP 937

Preferred Name

English

ANTHRA(1,9-CD)PYRAZOL-6(2H)-ONE, 7,10-DIHYDROXY-2-(2-((2-HYDROXYETHYL)AMINO)ETHYL)-5-((2-(METHYLAMINO)ETHYL)AMINO)-, DIHYDROCHLORIDE, MONOHYDRATE

Common Name

English

DUP-937

Code

English

NSC-355644

Code

English

7,10-Dihydroxy-2-[2-[(2-hydroxyethyl)amino]ethyl]-5-[[2-(methylamino)ethyl]amino]anthra[1,9-cd]pyrazol-6(2H)-one, dihydrochloride, monohydrate

Common Name

English

TELOXANTRONE HYDROCHLORIDE [MART.]

Common Name

English

TELOXANTRONE HYDROCHLORIDE [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2107